Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa

Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa
South Tulsa
10.0 out of 10, Exceptional, (34 reviews)
"This VRBO was cozy, clean, and the perfect little getaway spot!"
United States
Sara V.
The price is NZ$271
includes taxes & fees
19 Apr - 20 Apr
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa

"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8

"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8
South Tulsa
9.6 out of 10, Exceptional, (37 reviews)
"The kitchen was well equipped, and the beds were comfortable. The house was clean and we really enjoyed the fire place."
United States
Roy V.
The price is NZ$371
includes taxes & fees
16 Apr - 17 Apr
"The Big Cozy"- WiFi, Hot tub, Grill, Sleeps 8

Super cute studio apartment south of Tulsa! Newly renovated and ready to go!

Super cute studio apartment south of Tulsa! Newly renovated and ready to go!
Beggs
10.0 out of 10, Exceptional, (3 reviews)
"Great place great ppl will book again the following year."
United States
Flav
The price is NZ$239
includes taxes & fees
18 Apr - 19 Apr
Super cute studio apartment south of Tulsa! Newly renovated and ready to go!

Tulsa Area Home w/ Fenced Yard: Pets Welcome!

Tulsa Area Home w/ Fenced Yard: Pets Welcome!
3.0 star property
South Tulsa
The price is NZ$718
includes taxes & fees
20 Apr - 21 Apr
Tulsa Area Home w/ Fenced Yard: Pets Welcome!

Newly Built Modern Getaway on Private Acreage!

Newly Built Modern Getaway on Private Acreage!
Tulsa
10.0 out of 10, Exceptional, (6 reviews)
"Great place! Would definitely come back to this location!"
United States
Roger H.
The price is NZ$478
includes taxes & fees
17 Apr - 18 Apr
Newly Built Modern Getaway on Private Acreage!

Beautifully Remodeled 3-Bedroom Cozy Home!!

Beautifully Remodeled 3-Bedroom Cozy Home!!
Broken Arrow
9.6 out of 10, Exceptional, (50 reviews)
"The house was in a great location and we loved the floor plan. "
United States
Samantha S.
The price is NZ$409
includes taxes & fees
20 Apr - 21 Apr
Beautifully Remodeled 3-Bedroom Cozy Home!!

Scandi Home by Turnpike - KING Bed, Fast WiFi

Scandi Home by Turnpike - KING Bed, Fast WiFi
Broken Arrow
10.0 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay. It was clean, the house was equipped with everything we needed. Would certainly book again for future Oklahoma visits."
United States
Melissa B.
The price is NZ$535
includes taxes & fees
29 Apr - 30 Apr
Scandi Home by Turnpike - KING Bed, Fast WiFi

Nivi's Niche - Relaxing Retreat for the Whole Family!

Nivi's Niche - Relaxing Retreat for the Whole Family!
Broken Arrow
9.6 out of 10, Exceptional, (29 reviews)
"We had a great week while our wood floors were being redone in our house."
United States
Rob B.
The price is NZ$681
includes taxes & fees
20 Apr - 21 Apr
Nivi's Niche - Relaxing Retreat for the Whole Family!

Spacious 5-bedroom house, 2 living areas, in Tulsa, centralized location!

Spacious 5-bedroom house, 2 living areas, in Tulsa, centralized location!
South Tulsa
9.2 out of 10, Wonderful, (19 reviews)
"Nice, roomy place in the perfect location for visiting family in the area. Love the bunk area for the kids. Would definitely stay again."
United States
Bobby G.
The price is NZ$830
includes taxes & fees
16 Apr - 17 Apr
Spacious 5-bedroom house, 2 living areas, in Tulsa, centralized location!

New! 5/3 with Hot Tub, Arcade, Playground, Coffee bar, Large TV and Dining Table

New! 5/3 with Hot Tub, Arcade, Playground, Coffee bar, Large TV and Dining Table
South Tulsa
9.8 out of 10, Exceptional, (15 reviews)
"My family had a relaxing and comfortable stay. Great property, great location, we would stay here again when we're in the area!"
United States
Cerenity C.
The price is NZ$969
includes taxes & fees
20 Apr - 21 Apr
New! 5/3 with Hot Tub, Arcade, Playground, Coffee bar, Large TV and Dining Table

Serene Haven near Downtown Tulsa

Serene Haven near Downtown Tulsa
South Tulsa
8.6 out of 10, Excellent, (12 reviews)
"The place was perfect "
United States
Jennifer F.
Serene Haven near Downtown Tulsa

King Suite-4 Bedroom-Brookside-Riverside

King Suite-4 Bedroom-Brookside-Riverside
South Tulsa
9.0 out of 10, Wonderful, (13 reviews)
"Yes the stay was awesome!"
United States
Gavin H.
The price is NZ$537
includes taxes & fees
16 Apr - 17 Apr
King Suite-4 Bedroom-Brookside-Riverside

Charming and unique upscale 1-bedroom apartment in downtown Okmulgee

Charming and unique upscale 1-bedroom apartment in downtown Okmulgee
Okmulgee
Charming and unique upscale 1-bedroom apartment in downtown Okmulgee

Great Value! Comfortable Suite in Tulsa | Free Breakfast + Fitness Center + Seasonal Outdoor Pool

Great Value! Comfortable Suite in Tulsa | Free Breakfast + Fitness Center + Seasonal Outdoor Pool
Tulsa
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful time and will definitely book again"
United States
Stacy D.
The price is NZ$317
includes taxes & fees
29 Apr - 30 Apr
Great Value! Comfortable Suite in Tulsa | Free Breakfast + Fitness Center + Seasonal Outdoor Pool

5 star single level home, 4 bdrm, 3 bath + private office and great backyard!

5 star single level home, 4 bdrm, 3 bath + private office and great backyard!
Bixby
10.0 out of 10, Exceptional, (95 reviews)
"House was beautiful! "
United States
Jennifer H.
The price is NZ$574
includes taxes & fees
27 Apr - 28 Apr
5 star single level home, 4 bdrm, 3 bath + private office and great backyard!

Paradise awaits. Southern Hills/ORU/River Spirit

Paradise awaits. Southern Hills/ORU/River Spirit
South Tulsa
10.0 out of 10, Exceptional, (11 reviews)
"We loved our stay here! The place was bigger than I expected and comfortably accommodated my family and I. It also had all the baby gear we needed for our infant."
United States
Valeria C.
The price is NZ$769
includes taxes & fees
27 Apr - 28 Apr
Paradise awaits. Southern Hills/ORU/River Spirit

We're All Mad Here! - A Wonderland Escape in Tulsa

We're All Mad Here! - A Wonderland Escape in Tulsa
South Tulsa
9.6 out of 10, Exceptional, (8 reviews)
"THE ALICE AND WONDERLAND THEME WAS CUTE AND A EXPERIENCE. COMFY BED. QUITE NEIGHBORHOOD, CLOSE TO EVERYTHING"
United States
Phyllis E.
The price is NZ$482
includes taxes & fees
23 Apr - 24 Apr
We're All Mad Here! - A Wonderland Escape in Tulsa

Southern Hills Stunner! 3bd/2bth

Southern Hills Stunner! 3bd/2bth
South Tulsa
9.8 out of 10, Exceptional, (11 reviews)
"The house was great and would definitely stay there again!"
United States
Chris H.
The price is NZ$682
includes taxes & fees
16 Apr - 17 Apr
Southern Hills Stunner! 3bd/2bth

Tulsa Area Home w/ Fenced Yard: Pets Welcome!

Tulsa Area Home w/ Fenced Yard: Pets Welcome!
South Tulsa
10.0 out of 10, Exceptional, (1 review)
The price is NZ$635
includes taxes & fees
28 Apr - 29 Apr
Tulsa Area Home w/ Fenced Yard: Pets Welcome!

Enjoy Comfort On 66th

Enjoy Comfort On 66th
South Tulsa
8.0 out of 10, Very good, (8 reviews)
"I loved it. My host was accommodating and made it easy for me to contact them. The neighborhood was quiet and decent. The decoration in the home was nice and the beds were very comfortable to sleep in. My favorite area was the dining area with the most comfortable sitting chairs I’ve ever sat in at a table to eat. The home was roomy with the three bedrooms far apart from each so that was a plus as well. It was great!"
United States
Crystal T.
The price is NZ$500
includes taxes & fees
4 May - 5 May
Enjoy Comfort On 66th
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as NZ$271 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

7,000 Sqft At 'The Columns' Estate In South Tulsa: This holiday home rental outside of Winchester is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

Explore the area and family-friendly sights such as Oklahoma Aquarium, or get out into nature at a spot like Hawthorn Park. In the wider area, you’ll find Oklahoma State University Institute of Technology and Bixby Library.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip or a small group gathering.